The Wingman
by Amethyst Beloved
Summary: The origins of the Winston and Miles friendship that leads into a missing moment from 1410: Hero vs Villain where Winston is confused about Miles' breakup with Tristan.


When five-year-old Winston entered preschool, the shy boy didn't know a soul. That would soon change when a dark haired boy with "Star Wars" scrawled over his school bag rushed up to him and asked if he would deliver a note to the pretty redhead with pigtails on the other side of the school yard. When Winston noticed the boy holding hands with the same girl by the end of the day, he flashed him a winning smile and gave him the thumbs up.

However, the blossoming romance was short lived. A couple of days later she pretended that the boy no longer existed, not that he seemed to care. Winston's curiosity got the best of him as he approached him during recess.

"What happened to that girl? Did she have cooties?"

"She wanted me to come to her tea party. I told her that l'd rather play video games."

"I love video games!"

"Great! Wanna come over after school?"

"I have to ask my parents first. I'm Winston Chu, by the way."

The boy's eyes lit up.

"Like Chewbacca!"

Winston gave him a confused look.

"I'm Miles. And we're gonna be best friends, Chewy. I just know it!"

"Yeah... about that nickname..."

Flash forward to one decade later, and the boys have gotten into all kinds of trouble. But like the nickname, the friendship was there to stay. Winston took on the role as wingman and never looked back as he accomplished tasks such as being a lookout for teachers or jealous ex-boyfriends while Miles was busy making out with a girl, or being the go-between if Miles would inadvertently do the wrong thing and make the relationship go awry. From partying hard to nursing hangovers, the two were together through thick and thin.

Winston figured that there was nothing Miles could do that could ever shock him. The fact held true until the night of the thunderstorm that changed everything. There was a bit of turbulance between them, but they managed to get back on smooth terms.

Unfortunately, this was not the case for Miles and Tristan as they took their seats in History class. Tristan was trying so desparately to win Miles back that Winston couldn't help but feel sorry for him. Going against Wingman Code, he actually encouraged the blond to not try so hard if Miles was shutting him out. If he were to say such a thing to a fragile girl, those words would definitely reduce her to tears. But Tristan was too determined.

"Chewy, can you hold back for a second?"

Class was dismissed, and Winston turned to look at Miles who had his jaw clenched and arms stiffly at his side

"I need my wingman. Can you make sure that Tristan stays at his locker before lunch period is over until you see me?"

"No problem-o, bro," Winston replied, feeling a bit relieved for Tristan.

Towards the end of the break, Winston smiled over the text he receieved from Frankie gushing about Tristan's romantic grand gesture. He took the hint that he now had to organize an elaborate date to not be shown up. Just as he was going to ask for Tristan's advice, he couldn't help but notice the downhearted look on the boy's face. This didn't make any sense. Why would Miles still put up a cold front? At least he was cooking something up to make things right.

Or so he thought.

Just as promised, Miles was there. But instead of trying to win Tristan over, he was standing right in his line of vision giving a longing look to his ex. With a heavy heart Winston had no choice but to point out the obvious. Upon witnessing the scene, Tristan quickly closed his locker and surried away. Winston marched towards Miles.

"What's your problem?" he hissed, trying not to make a scene in the crowded hallway despite feeling furious with the way Miles was treating Tristan. "You asked me to stall Tristan at his locker long enough for him to see your stupid lovesick smile?"

Miles wasn't smiling anymore. In fact he looked sadder than ever.

"Fine. Live your life. I can't tell you what to do. So I guess you need my help to get Maya back, right?"

"No."

"There's another girl?"

"No."

Wiston tried not to make a face as he choked out his next couple of words.

"Another… _dude_?"

Miles slowly shook his head.

"Okay. Well, let's go over to Chompy Chicken to drown your sorrows, then."

"No. Not that."

That was when the alarm bells started to ring. Winston realized that this was no ordinary break up. He's seen Miles bounce back from relationships before. Even after his bitter break-up with Maya he was still able to go on as a funtioning human being by teasing Frankie and what not. There was something different. This wasn't just the end of Miles' relationship with Tristan. No, this was the end of Miles Hollingsworth, lover boy extraordinaire. Gone was the spark in his eye that would help heal his wounds before propeling him to his next conquest.

"How about a mind-numbing video game marathon, then," Winston slowly suggested as a last resort. "Nothing else but us and the good TV."

To his relief, Miles finally nodded his head.

Winston wasn't sure what was going on. All he knew was that Miles needed a friend now more than ever.


End file.
